Herbicidal sulfonamides

ABSTRACT

This invention relates to ortho(acyloxy)benzenesulfonamides and their use as herbicides.

This is a continuation, of application Ser. No. 168,353, filed July 11, 1980, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to ortho(acyloxy)benzenesulfonamides and their use as herbicides.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (I) and their use as general or selective herbicides: ##STR1## wherein R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

Compounds of Formula (II), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974): ##STR2## wherein R is pyridyl.

In U.S. Pat. No. 4,127,405, compounds are disclosed of the general formula: ##STR3## wherein R₁ is ##STR4## R₃ and R₆ are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) -- or CH₃ CH₂ S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Z is methyl or methoxy; or their agriculturally suitable salts; provided that:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ is other than hydrogen and at least two of R₃, R₄, R₆ and R₇ must be hydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other than hydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine or methyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ and R₆ must be hydrogen.

In particular, the patent discloses orthosubstituted compounds wherein the substitution is C₁ -C₄ alkyl.

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.

A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formula I, to compositions containing them, and to their method of use as herbicides having both pre- and post-emergence activity: ##STR5## wherein P is ##STR6## R₁ is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, C₁ -C₃ alkoxy, CF₃ or ##STR7## R₂ is H, CH₃ or Cl; R₃ is H; C_(1-C) ₅ alkyl; C₂ -C₃ alkenyl; C₂ -C₃ alkynyl; C₁ -C₄ alkyl substituted with 1-3 substituents selected from 0-3 F, 0-3 Cl, 0-3 Br, and OCH₃ ; C₂ -C₃ alkenyl substituted with Cl; C₃ -C₆ cycloalkyl; or ##STR8## R₄ is C₁ -C₆ alkyl; C₃ -C₄ alkenyl; C₃ -C₆ cycloalkyl; C₅ -C₆ cycloalkyl substituted with CH₃ ; ##STR9## R₅ is C₁ -C₆ alkyl or ##STR10## R₆ and R₇ are independently H, NO₂, CH₃, Cl or OCH₃ ;

R₈ is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, CN, SO₂ CH₃, OCH₃, SCH₃ or CF₃ ;

R₉ is H or C₁ -C₃ alkyl;

R₁₀ is H, CH₃ or Cl;

A is ##STR11## X is H, Cl, Br, CH₃, CH₃ CH₂, C₁ -C₃ alkoxy, CF₃, CH₃ S or CH₃ OCH₂ ;

Y is CH₃ or CH₃ O;

Z is N, CH, C--Cl, C--BR, C--CN, C--CH₃, --C--CH₂ CH₃, C--CH₂ CH₂ Cl or C--CH₂ CH═CH₂ ;

Y' is H, CH₃, OCH₃ or Cl; and

Q is O or CH₂ ;

and their agriculturally suitable salts.

Preferred in increasing order and for reasons of higher activity and/or lower cost and/or greater ease of synthesis are those compounds of:

(1) The generic scope where Z is N, CH, C--Cl, C--CN, C--Br or C--CH₃ ;

(2) Preferred 1 where Z is CH or N and X is CH₃ or OCH₃ ;

(3) Preferred 2 where A is ##STR12## (4) Preferred 3 where R₁ is H; (5) Preferred 4 where R₂ is H; and

(6) Preferred 5 where R₃, R₄ and R₅ are C₁ -C₃ alkyl.

Specifically preferred for reasons of highest herbicidal activity and/or lowest cost and/or greatest ease in synthesis are:

3,5-dichloro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide; and

3,5-dichloro-2-hydroxy-N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl)benzenesulfonamide.

The following compounds of Formula II are novel and useful as intermediates in the preparation of the herbicides of this invention. ##STR13##

Synthesis

Compounds of Formula I can be made by one of the methods (1 or 2) shown below, depending on the identity of group P: ##STR14## wherein P₁ is ##STR15## R_(3a) is H; C₁ -C₅ alkyl; C₁ -C₄ alkyl substituted with 1-3 substituents selected from 0-3 F, 0-3 Cl, 0-3 Br and OCH₃ ; C₄ -C₆ cycloalkyl; or ##STR16## A, R₁, R₂, R₅, R₆ and R₇ are as defined in Formula I.

The reaction is best carried out in inert aprotic organic solvents such as methylene chloride, tetrahydrofuran or acetonitrile, at ambient pressure and temperatures from 0° to 80° C. The mode of addition is not critical; however, it is preferred to add the aminoheterocycle to a stirred solution of the sulfonyl isocyanate, thereby lessening the chance of reaction between the aminoheterocycle and group P.

The reaction is generally exothermic. In some cases, the desired product is insoluble in the reaction medium and crystallizes from it in pure form. Products soluble in the reaction mixture are isolated by evaporation of the solvent, trituration of the residue with solvents in which it is sparingly soluble, such as 1-chlorobutane, ethyl ether or pentane, and filtration.

The intermediate sulfonyl isocyanates of Formula IV can be prepared from the parent sulfonamides of Formula VII as shown in Equation 1b. Reaction with phosgene in the pressure of n-butyl isocyanate and a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane (DABCO) at reflux in a solvent such as chlorobenzene or xylenes, according to the procedure of H. Ulrich and A. A. Y. Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Acadamic Press, New York and London, W. Foerst, Ed., affords the sulfonyl isocyanates IV. ##STR17##

A mixture of the appropriate sulfonamide VII, an alkyl isocyanate such as butyl isocyanate and a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane (DABCO) in xylene, chlorobenzene or other inert solvent of sufficiently high boiling point (e.g. ≧135°) is heated to approximately 135°. Phosgene is added to the mixture until an excess of phosgene is present as indicated by a drop in the boiling point. The mixture is heated further to drive off excess phosgene. The mixture is cooled and filtered to remove insoluble by-products under a dry stream of nitrogen or air. The solvent and alkyl isocyanate are distilled off in vacuo leaving a residue which is the crude sulfonyl isocyanate IV. Alternatively, the sulfonyl isocyanate can be made by the method of Ulrich, et al., J. Org. Chem. 34, 3200 (1969), as described after Equation 2b.

Sulfonamides of Formula VII can be prepared by several different methods known in the literature. o-Hydroxybenzenesulfonamides of Formula VIII can be reacted with an appropriate reagent E [an acyl halide or anhydride, i.e., ##STR18## as shown in Equation 1c. ##STR19##

These reactions are best carried out in inert aprotic solvents such as methylene chloride, tetrahydrofuran or acetonitrile at 0°-80° C. One equivalent of the acyl halide or anhydride is used with one equivalent of a tertiary amine such as pyridine, triethylamine or 4-dimethylaminopyridine. Isolation of the product is achieved by evaporation of the solvent and recrystallization from suitable solvents or chromatography on silica gel.

Certain sulfonyl chlorides of Formula X can best be prepared by chlorosulfonation of a substituted phenol, according to the teaching of H. T. Clarke, et al., Org. Syn. Coll. Vol. 1, 2nd Ed., 1941, p. 85. ##STR20##

Alternatively, o-hydroxybenzenesulfonamides of Formula XII, and thus some of the sulfonamides of Formula VII, can be prepared by cleavage of an appropriately substituted o-methoxybenzenesulfonamide of Formula XI with sodium thioethoxide in boiling dimethylformamide, according to the teaching of G. I. Feutrill and R. N. Mirrington, Tetrahedron Letters, 1327 (1970). This reaction is shown in Equation 1e. ##STR21## wherein R_(1a) is H, F, Cl, Br or C₁ -C₃ alkyl; and

R₂ is as defined for compound I.

The reaction is best carried out by addition of the o-methoxybenzenesulfonamide XI in dry dimethylformamide (DMF) to a solution of sodium thioethoxide in DMF, prepared by the action of a strong base such as sodium hydride on ethanethiol in DMF. The reaction mixture is boiled under reflux (140° C.) for 3 hours, cooled and the solvent is decanted and/or stripped from the sodium salt of the product XIX. Suspension in water, acidification, extraction with an appropriate solvent such as ethyl acetate, chloroform or diethyl ether and removal of the solvent in vacuo leaves compounds of Formula XII.

o-Methoxybenzenesulfonamides of Formula XI can best be prepared by reaction of the corresponding o-methoxybenzenesulfonyl chlorides with anhydrous ammonia in diethyl ether or tetrahydrofuran or ammonium hydroxide solution. Certain o-methoxybenzenesulfonyl chlorides can be prepared by the melhod shown in Equation 1f. Diazotization of the appropriate o-methoxyaniline with sodium nitrate in dilute sulfuric acid is followed by reaction of the diazonium salt with sulfur dioxide and cupric chloride in acetic acid and hydrochloric acid at 40° C. with n-butyl chloride as a co-solvent, according to the teaching of Ukr. Khim. Zh. 35(8) 821-3 (1969) [CA72 43066e(70)]. ##STR22##

Alternatively, m-methoxybenzenesulfonyl chlorides XVI can be prepared as shown in Equation 1g, according to the teachings of J. E. Cooper and J. M. Paul, J. Org. Chem. 35, 2046 (1970) and H. Graafland, et al., J. Am. Chem. Soc. 101, 6981 (1979), from 2-hydroxyanisole derivatives XV. ##STR23## wherein R_(1b) is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, C₁ -C₃ alkoxy or CF₃ ; and

R₂ is as defined in Formula I.

The choice of any of the above methods outlined for the preparation of compounds of Formula VII would depend upon the nature of the aromatic substituents, and would be obvious to one skilled in the art.

Many of the compounds of Formula I can be prepared as shown in Equation 2a by reaction of an appropriately substituted o-hydroxybenzenesulfonylurea II with an appropriate acylating reagent G [an acyl halide or anhydride, or an isocyanate, i.e., ##STR24## wherein

G is an acylating reagent for addition of the group ##STR25## P₂ is ##STR26## R_(3b) is C₁ -C₅ alkyl; C₂ -C₃ alkenyl; C₂ -C₃ alkynyl; C₁ -C₄ alkyl substituted with 1-3 substituents selected from 0-3 F, 0-3 Cl, 0-3 Br and OCH₃ ; C₂ -C₃ alkenyl substituted with Cl; C₃ -C₆ cycloalkyl; or ##STR27## A, R₁, R₂, R₄, R₅, R₆, R₇, R₈ and R₉ are as defined in Formula I.

The reaction of Equation 2a can be carried out in inert solvents such as tetrahydrofuran (THF) or dioxane at about -10° to 80°. At least one equivalent of sodium hydride is added to compound II dissolved or suspended in the solvent. When the evolution of hydrogen is substantially complete, one equivalent of reagent G is added to the reaction mixture which is then allowed to come to room temperature. Isolation of the product XVII can be accomplished by evaporation of the solvent and optional further purification by recrystallization from suitable solvents or by column chromatography on silica gel.

Many of the o-hydroxybenzenesulfonylureas of Formula II can be prepared by the method outlined in Equation 2b. ##STR28## wherein Bz is benzyl;

R_(1c) is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, C_(1-C) ₃ alkoxy or CF₃ ; and

R₂ and A are as defined in Formula I.

The 2-(benzyloxy)anilines XIX [Chem. Berichte 58, 79 (1925)] can be diazotized in the usual manner and converted to the sulfonyl chloride by coupling with sulfur dioxide and cuprous chloride. Reaction of the sulfonyl chloride with concentrated ammonium hydroxide solution affords the 2-(benzyloxy)benzenesulfonamides XIX. The corresponding sulfonyl isocyanates XX can be prepared by the method of Ulrich, et al., J. Org. Chem. 34, 3200 (1969). The sulfonamide is boiled under reflux with an excess of thionyl chloride which functions as a reactant and solvent. An overnight reaction period is generally sufficient. The thionyl chloride is evaporated and the residue dissolved in an inert solvent such as toluene or xylene, contacted with a catalytic amount of pyridine, then with at least one equivalent of phosgene. The mixture is heated to about 60°-140°, with 80°-100° preferred. The mixture containing the sulfonyl isocyanate can be used directly for the next reaction step or the sulfonyl isocyanate can be isolated by filtration and evaporation of the solvent. The isocyanate can be redissolved in a suitable solvent such as methylene chloride, toluene or acetonitrile and the solution contacted with the amino heterocycle, ANH₂ to provide the 2-(benzyloxy)sulfonylurea XXI. Conveniently, the starting reaction temperature is ambient but can be varied from about 0° to 100° if desired. The product can be isolated by filtration if it precipitates from the reaction mixture, otherwise, the solvent can be evaporated and the residual product obtained thereby, with optional further purification obtained by trituration with an organic solvent in which the product is sparingly soluble, such as diethyl ether or 1-chlorobutane and filtration.

The benzyl protecting group can be removed by treatment of the 2-(benzyloxy)benzenesulfonylurea with trifluoroacetic acid according to the teaching of J. P. Marsh and L. Goodman, J. Org. Chem. 30, 2491 (1965). The benzyl ether is dissolved in trifluoroacetic acid and heated from 50°-80° C. for 0.5-3 hours. The reaction progess can be monitored by proton magnetic resonance spectrum and halted upon complete cleavage of the benzyl ether. The trifluoroacetic acid is evaporated in vacuo and the residue can be stirred with solvents such as 1-chlorobutane or ethyl ether to help purify the product XXII. Optional further purification may be performed by dissolving the product in a solvent such as acetone and reprecipitation with a non-polar solvent such as hexane, or by column chromatography on silica gel.

The synthesis of heterocyclic amines has been reviewed in "The Chemistry of Heterocyclic Compounds" a series published by Interscience Publ., New York and London. 2-Aminopyrimidines are described by D. J. Brown in The Pyrimidines, Vol. XVI of this series. The 2-amino-1,3,5-triazines are reviewed by K. R. Huffman and in the Triazines of this same series. The synthesis of triazines are also described by F. C. Schaefer, U.S. Pat. No. 3,154,547 and by K. R. Huffman and F. C. Schaeffer, J. Org. Chem. 28, 1816-1821 (1963).

The preparation of the aminoheterocycles described by the following formula varies according to the definition of Y₁ and Q. ##STR29##

Braker, Sheehan, Spitzmiller and Lott, J. Am. Chem. Soc. 69, 3072 (1947) describe the preparation of 6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-amine by the following sequence of reactions. ##STR30##

Similarly, 6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine can be prepared by the condensation of 2-acetylcyclopentanone with guanidine carbonate, but preferably under acidic conditions, removing the water formed. ##STR31##

Shrage and Hitchings, J. Org. Chem. 16, 1153 (1951) describe the preparation of 5,6-dihydro-4-methylfuro-[2,3-d]pyrimidin-2-amine by the following sequence of reactions. ##STR32##

5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-amine can be prepared by the method of Braker et al., J. Am. Chem. Soc. 69, 3072 (1947), using 5,6-dihydro-4-hydroxyfuro[2,3-d]pyrimidin-2-amine [Svab, Budesinski and Vavrina, Collection Czech. Chem. Commun. 32, 1582 (1967)]. ##STR33##

Caldwell, Kornfeld and Donnell, J. Am. Chem. Soc. 63, 2188 (1941), describe the preparation of 6,7-dihydro-5H-cyclopentapyrimidin-2-amine by the following sequence of reactions. ##STR34##

Fissekis, Myles and Brown, J. Org. Chem. 29, 2670 (1964), describe the preparation of 2-amino-4-hydroxy-5-(2-hydroxyethyl)pyrimidine which can be converted to 5,6-dihydrofuro[2,3-d]pyrimidin-2-amine by dehydration. ##STR35##

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared by a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation to another. Cationic exchange can be effected by direct treatment of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water, e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water soluble, e.g., a potassium, sodium or calcium salt.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The following examples illustrated preparation of compounds of this invention, wherein temperatures are in degrees centigrade.

EXAMPLE 1 a. 3,5-Dichloro-2-hydroxybenzenesulfonamide

A solution of 26.1 gm (0.1 mole) 3,5-dichloro-2-hydroxybenzenesulfonyl chloride in 400 ml dry tetrahydrofuran was cooled to 0° with an ice bath, and 11 ml (0.5 mole) anhydrous ammonia was added dropwise, with stirring. The rate of addition was sufficiently slow so as to keep the temperature of the reaction medium less than 10°. The mixture was stirred for 1.5 hours at 0° then slowly warmed to room temperature. The solvent was removed in vacuo and the residue was treated with 100 ml H₂ O. A small amount of insoluble by-product was filtered off and then the aqueous solution was acidified to pH=2.0 with 1 N HCl solution. Filtration of the resulting white precipitate and drying of the precipitate at 50° under vacuum gave 23.6 gm (97%) white solid, m.p. >225°. The infrared spectrum showed strong absorption at 3300, 1540, 1450 and 1320 cm⁻¹, and the nuclear magnetic resonance spectrum showed a broad singlet at 7.2δ, 3 protons, and a doublet of doublets at 7.8δ, 2 protons. These data are consistent with the desired product.

b. 2-Acetoxy-3,5-dichlorobenzenesulfonamide

3,5-Dichloro-2-hydroxybenzenesulfonamide (10.8 gm, 0.045 mole) was dissolved in 100 ml tetrahydrofuran containing 3.6 gm (0.045 mole) pyridine. The mixture was cooled to -10° by an ice bath and then 4.6 ml (0.045 mole) acetic anhydride dissolved in 10 ml tetrahydrofuran was added dropwise, with stirring, over 30 minutes. The mixture was then warmed to ambient temperature and stirred for 4 to 5 hours. The solvent was removed in vacuo and treated with 500 ml water. The aqueous solution was extracted three times with 250 ml of diethyl ether. The combined organic extracts were washed 3 times with 100 ml each 1 N hydrochloric acid and once with 200 ml brine. After drying over Na₂ SO₄, the ether was removed in vacuo to yield 10.8 gm (84.5%) of a white solid, m.p. 139°-143°. The infrared spectrum showed strong absorbances at 3400 (NH₂), ##STR36## 1620, 1570, 1360, 1120-1200 cm⁻¹ and the nuclear magnetic resonance spectrum (in acetone-d₆) showed a singlet at 2.33δ, 3H; broad singlet at 5.2δ,2H; and a singlet at 7.7δ, 2H, corresponding to the methyl, sulfonamide and aromatic protons, respectively, of the desired product.

c. N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-acetoxy-3,5-dichlorobenzenesulfonamide

A mixture of 6.0 gm (0.02 mole) 2-acetoxy-3,5-dichlorobenzenesulfonamide, 0.1 gm 1,4-diaza[2.2.2]bicyclooctane (DABCO), 2.8 ml (0.025 mole) n-butyl isocyanate and 50 ml dry xylenes was heated to reflux and maintained at that temperature for 1 hour. Phosgene (0.03 mole, 1.3 ml) was then added dropwise, so as to maintain the reaction temperature >130°. The reaction mixture was boiled under reflux for 3 hours after addition of phosgene, then cooled and filtered. The solvent was removed in vacuo and the residue was dissolved in 20 ml of methylene chloride and added directly to a stirred solution of 2-amino-4-methoxy-6-methylpyrimidine in 10 ml methylene chloride. The reaction was protected from atmospheric moisture and stirred overnight. Filtration of the solution removed excess starting material and the solution was evaporated to a residue. The residue was washed with 1-butyl chloride and filtered, giving 1.4 g (0.003 mole, 22% yield) of the sulfonylurea product. The nuclear magnetic resonance of the product shows peaks as follows: (singlet, 2.0δ, 3H, singlet, 2.2δ, 3H; singlet, 3.9δ, 3H; singlet, 6.1δ, 1H; 7.5-8.2δ, multiplet, 2H; br singlet, 8.6δ, 1H), consistent with the desired product.

EXAMPLE 2 N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide a. 2-(Benzyloxy)benzenesulfonamide

To 148 ml of concentrated hydrochloric acid and 45 ml of acetic acid, maintained at <10°, was added 39.2 g of 2-(benzyloxy)aniline [See Berichte, 58, 79 (1925)]. White solid formed. Sufficient additional acetic acid was added to render the mixture stirrable. While temperature was 0° to 3°, a solution of 28 g of sodium nitrite in 75 ml of water was dripped into it. The mixture was kept at 5° to 10° for 15 minutes, then added to a mixture of 5.2 g of cuprous chloride, 37 ml of sulfur dioxide and 211 ml of acetic acid at 3°. Next, 290 ml of butyl chloride was added and the mixture allowed to warm to ambient temperature. After 16 hours, the mixture was diluted with water and the organic layer washed with water and dilute sodium bicarbonate solution until the washings were basic. The mixture was then dried (MgSO₄) and evaporated to an oil (A). The effervescing aqueous portion (from which the butyl chloride solution had been removed) was depositing an oil; it was then treated portionwise with sodium bisulfite over several hours. After about 16 hours the oil was extracted into butyl chloride and the butyl chloride solution washed, dried and evaporated, providing an oil (B). Oils A and B are 2-(benzyloxy)benzenesulfonyl chloride. To oils A and B was added an excess of concentrated aqueous ammonia, the mixture was swirled and a white solid was observed. The solid was filtered off and extracted with hot butyl chloride; upon cooling, the extract precipitated 2-(benzyloxy)benzenesulfonamide as a white solid, m.p. 127°-129°.

b. N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-(benzyloxy)benzenesulfonamide

A solution of 5.4 g of the sulfonamide (from a, above) in 40 ml of thionyl chloride was boiled under reflux for 39 hours. The solution was evaporated to an oil and the oil dissolved in 40 ml of a 13.8% phosgene solution in toluene. Three drops of pyridine was added and the mixture heated for 2 hours at 85° under phosgene reflux. The mixture was then filtered and evaporated to an oil, 2-(benzyloxy)benzensulfonyl isocyanate. The infrared spectrum showed a strong absorption peak at 2230 cm⁻¹, characteristic of a sulfonyl isocyanate.

Addition of 2.52 g of 2-amino-4,6-dimethylpyrimidine to a solution of the isocyanate in acetonitrile resulted in an exothermic reaction and precipitation of a white solid. After 2 hours, the solid was filtered off and washed with acetonitrile and butyl chloride, leaving N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(benzyloxy)benzenesulfonamide as a white solid, m.p. 218° (dec.). The infrared spectrum showed an absorption peak at 1700 cm⁻¹ for the urea carbonyl group. The mass spectrum showed ##STR37## and m/e 91 (PhCH₂ ⁺).

c. N-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide

A stirred solution of 0.5 g of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(benzyloxy)benzenesulfonamide (from b, above) in 20 ml of trifluoroacetic acid was boiled under reflux for 1.5 hours. The proton magnetic resonance spectrum indicated complete cleavage of the benzyl ether. The trifluoroacetic acid was evaporated in vacuum and the oily residue stirred with water and diethyl ether, providing white solid. The solid was dissolved in acetone and reprecipitated by dilution of the solution with hexane, yielding N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide as a white solid, m.p. ca. 180°. The mass spectrum showed a molecular ion, m/e 322; ##STR38## and no m/e 91 (no Ph--CH₂ ⁺).

By the procedures of Examples 1 and 2 and the methods discussed, the following compounds can be prepared by one skilled in the art.

                  TABLE I                                                          ______________________________________                                          ##STR39##                                                                     R.sub.1  R.sub.2 X           Y     Z                                           ______________________________________                                         H        H       CH.sub.3    CH.sub.3                                                                             CH                                          H        H       CH.sub.3 O  CH.sub.3                                                                             CH                                          H        H       CH.sub.3 O  CH.sub.3 O                                                                           CH                                          5-F      H       CH.sub.3    CH.sub.3                                                                             CH                                          3-Cl     H       CH.sub.3    CH.sub.3                                                                             CH                                          4-Cl     H       CH.sub.3    CH.sub.3                                                                             CH                                          5-Cl     3       CH.sub.3    CH.sub.3                                                                             CH                                          6-Cl     H       CH.sub.3    CH.sub.3                                                                             CH                                          5-Br     H       CH.sub.3    CH.sub.3                                                                             CH                                          3-CH.sub.3                                                                              H       CH.sub.3    CH.sub.3                                                                             CH                                          6-CH.sub.3                                                                              H       CH.sub.3    CH.sub.3                                                                             CH                                          6-(CH.sub.3).sub.2 CH                                                                   H       CH.sub.3    CH.sub.3                                                                             CH                                          5-NO.sub. 2                                                                             H       CH.sub.3    CH.sub.3                                                                             CH                                          5-CH.sub.3 O                                                                            H       CH.sub.3    CH.sub.3                                                                             CH                                          5-(CH.sub.3).sub.2 CHOH                                                                     CH.sub.3    CH.sub.3                                                                               CH                                            5-CF.sub.3                                                                              H       CH.sub.3    CH.sub.3                                                                             CH                                          5-OCOCH.sub.3                                                                           H       CH.sub.3    CH.sub.3                                                                             CH                                          3-CH.sub.3                                                                              5-CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                             CH                                          3-Cl     5-Cl    CH.sub.3    CH.sub.3                                                                             CH                                          3-Cl     5-CH.sub.3                                                                             CH.sub.3    CH.sub.3                                                                             CH                                          H        H       CH.sub.3    CH.sub.3                                                                             N                                           H        H       CH.sub.3 O  CH.sub.3                                                                             N                                           H        H       CH.sub.3 O  CH.sub.3 O                                                                           N                                           H        H       CH.sub.3    CH.sub.3                                                                             CCl                                         H        H       CH.sub.3    CH.sub.3                                                                             CBr                                         H        H       CH.sub.3    CH.sub.3                                                                             CCN                                         H        H       CH.sub.3    CH.sub.3                                                                             CCH.sub.3                                   H        H       CH.sub.3    CH.sub.3                                                                             CC.sub.2 H.sub.5                            H        H       CH.sub.3    CH.sub.3                                                                             CCH.sub.2 CH.sub.2 Cl                       H        H       CH.sub.3    CH.sub.3                                                                             CCH.sub.2 CHCH.sub.2                        H        H       H           CH.sub.3                                                                             CH                                          H        H       Cl          OCH.sub.3                                                                            CH                                          H        H       Br          OCH.sub.3                                                                            CH                                          H        H       C.sub.2 H.sub.5                                                                            CH.sub.3                                                                             CH                                          H        H       CH.sub.3 CH.sub.2 CH.sub.2 O                                                               OCH.sub.3                                                                            CH                                          H        H       CF.sub.3    CH.sub.3                                                                             CH                                          H        H       CH.sub.3 S  CH.sub.3 O                                                                           CH                                          H        H       CH.sub.3 OCH.sub.2                                                                         CH.sub.3                                                                             CH                                          H        H       H           CH.sub.3                                                                             N                                           H        H       Cl          OCH.sub.3                                                                            N                                           H        H       Br          OCH.sub.3                                                                            N                                           H        H       C.sub.2 H.sub.5                                                                            CH.sub.3                                                                             N                                           H        H       CH.sub.3 CH.sub.2 CH.sub.2 O                                                               OCH.sub.3                                                                            N                                           H        H       CF.sub.3    CH.sub.3                                                                             N                                           H        H       CH.sub.3 S  CH.sub.3 O                                                                           N                                           H        H       CH.sub.3 OCH.sub.2                                                                         CH.sub.3                                                                             N                                           ______________________________________                                    

                  TABLE II                                                         ______________________________________                                          ##STR40##                                                                     R.sub.1     R.sub.2    Y'          Q                                           ______________________________________                                         3-Cl        5-Cl       H           O                                           3-Cl        5-Cl       CH.sub.3    O                                           3-Cl        5-Cl       OCH.sub.3   O                                           3-Cl        5-Cl       Cl          O                                           3-Cl        5-Cl       H           CH.sub.2                                    3-Cl        5-Cl       CH.sub.3    CH.sub.2                                    3-Cl        5-Cl       OCH.sub.3   CH.sub.2                                    3-Cl        5-Cl       Cl          CH.sub.2                                    H           H          H           O                                           H           H          CH.sub.3    O                                           H           H          OCH.sub.3   O                                           H           H          Cl          O                                           H           H          H           CH.sub.2                                    H           H          CH.sub.3    CH.sub.2                                    H           H          OCH.sub.3   CH.sub.2                                    H           H          Cl          CH.sub.2                                    ______________________________________                                    

                                      TABLE III                                    __________________________________________________________________________      ##STR41##                                                                     R.sub.1 R.sub.2                                                                            R.sub.3  X      Y   Z      m.p. (°C.)                       __________________________________________________________________________     H       H   H        CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   CH.sub.2CH                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   CH.sub.2CHCH.sub.2                                                                      CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   HCC      CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   CH.sub.3 CC                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   ClCH.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   BrCH.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   Cl.sub.3 C                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   Br.sub.3 C                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   F.sub.3 C                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   CH.sub.3 OCH.sub.2                                                                      CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   Cl(CH.sub.2).sub.4                                                                      CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   ClCHCH   CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   ClCH.sub.2 CHCH                                                                         CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR42##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR43##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR44##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR45##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR46##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR47##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR48##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR49##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR50##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR51##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR52##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   H        CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   CH.sub.2CH                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   CH.sub.2CHCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   HCC      CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   CH.sub.3 CC                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   ClCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   BrCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   Cl.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   Br.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   F.sub.3 C                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   CH.sub.3 OCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   Cl(CH.sub.2).sub.4                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   ClCHCH   CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   ClCH.sub.2 CHCH                                                                         CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR53##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR54##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR55##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR56##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR57##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR58##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR59##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR60##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR61##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR62##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H                                                                                   ##STR63##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             H       H   H        CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   CH.sub.2CH                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   CH.sub.2CHCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   HCC      CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   CH.sub.3 CC                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   ClCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   BrCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   Cl.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   Br.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   F.sub.3 C                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   CH.sub.3 OCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   Cl(CH.sub.2).sub.4                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   ClCHCH   CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   ClCH.sub.2 CHCH                                                                         CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR64##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR65##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR66##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR67##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR68##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR69##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR70##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR71##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR72##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR73##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H                                                                                   ##STR74##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             H       H   H        CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   CH.sub.2CH                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   CH.sub.2CHCH.sub.2                                                                      CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   HCC      CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   CH.sub.3 CC                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   ClCH.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   BrCH.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   Cl.sub.3 C                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   Br.sub.3 C                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   F.sub.3 C                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   CH.sub.3 OCH.sub.2                                                                      CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   Cl(CH.sub.2).sub.4                                                                      CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   ClCHCH   CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   ClCH.sub.2 CHCH                                                                         CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR75##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR76##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR77##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR78##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR79##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR80##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR81##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR82##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR83##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR84##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H                                                                                   ##STR85##                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              H       H   H        CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   CH.sub.2CH                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   CH.sub.2CHCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   HCC      CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   CH.sub.3 CC                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   ClCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   BrCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   Cl.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   Br.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   F.sub.3 C                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   CH.sub.3 OCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   Cl(CH.sub.2).sub.4                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   ClCHCH   CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   ClCH.sub.2 CHCH                                                                         CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR86##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR87##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR88##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR89##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR90##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR91##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR92##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR93##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR94##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR95##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H                                                                                   ##STR96##                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              H       H   H        CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   CH.sub.2CH                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   CH.sub.2CHCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   HCC      CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   CH.sub.3 CC                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   ClCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   BrCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   Cl.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   Br.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   F.sub.3 C                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   CH.sub.3 OCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   Cl(CH.sub.2).sub.4                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   ClCHCH   CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   ClCH.sub.2 CHCH                                                                         CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR97##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR98##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR99##                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR100##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR101##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR102##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR103##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR104##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR105##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR106##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H                                                                                   ##STR107##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               H        CH.sub.3                                                                              CH.sub.3                                                                           CH     173-175°                         3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.2CH                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                      CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               HCC      CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 CC                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               ClCH.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               BrCH.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               Cl.sub.3 C                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               Br.sub.3 C                                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               F.sub.3 C                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 OCH.sub.2                                                                      CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               Cl(CH.sub.2).sub.4                                                                      CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               ClCHCH   CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               ClCH.sub.2 CHCH                                                                         CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR108##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR109##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR110##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR111##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR112##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR113##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR114##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR115##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR116##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR117##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR118##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               H        CH.sub.3 O                                                                            CH.sub.3                                                                           CH     138-143°                         3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.2CH                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               HCC      CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 CC                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               ClCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               BrCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               Cl.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               Br.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub. 3                                                                          CH                                             3-Cl    5-Cl                                                                               F.sub.3 C                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 OCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               Cl(CH.sub.2).sub.4                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               ClCHCH   CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               ClCH.sub.2 CHCH                                                                         CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR119##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR120##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR121##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR122##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR123##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR124##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR125##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR126##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR127##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR128##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR129##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               H        CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH     186-189°                         3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               CH.sub.2CH                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               CH.sub. 2CHCH.sub.2                                                                     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               HCC      CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               CH.sub.3 CC                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               ClCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               BrCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               Cl.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               Br.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               F.sub.3 C                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               CH.sub.3 OCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               Cl(CH.sub.2).sub.4                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               ClCHCH   CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               ClCH.sub.2 CHCH                                                                         CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR130##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR131##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR132##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR133##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR134##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR135##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR136##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR137##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR138##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                                ##STR139##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR140##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-Cl                                                                               H        CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.2CH                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                      CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               HCC      CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.3 CC                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               ClCH.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               BrCH.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               Cl.sub.3 C                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               Br.sub.3 C                                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               F.sub.3 C                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.3 OCH.sub.2                                                                      CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               Cl(CH.sub.2).sub.4                                                                      CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               ClCHCH   CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               ClCH.sub.2 CHCH                                                                         CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR141##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR142##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                                ##STR143##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR144##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR145##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR146##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR147##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR148##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR149##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR150##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR151##                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                              -3-Cl   5-Cl                                                                               H        CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.2CH                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               HC C     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.3 CC                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               ClCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               BrCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               Cl.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               Br.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               F.sub.3 C                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               CH.sub.3 OCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               Cl(CH.sub.2).sub.4                                                                      CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               ClCHCH   CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               ClCH.sub.2 CHCH                                                                         CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR152##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR153##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR154##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR155##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR156##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR157##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR158##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR159##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR160##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR161##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                                ##STR162##                                                                             CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-Cl                                                                               H        CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               CH.sub.2CH                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               HC C     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               CH.sub.3 CC                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               ClCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               BrCH.sub.2                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               Cl.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               Br.sub.3 C                                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               F.sub.3 C                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               CH.sub.3 OCH.sub.2                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               Cl(CH.sub.2).sub.4                                                                      CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               ClCHCH   CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                               ClCH.sub.2 CHCH                                                                         CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR163##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR164##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR165##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR166##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR167##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR168##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR169##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR170##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR171##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR172##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-Cl                                                                                ##STR173##                                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              5-F     H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             4-Cl    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-Cl    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             6-Cl    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-Br    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             6-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-NO.sub.2                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-CH.sub.3 O                                                                           H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-CF.sub.3                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-OCOCH.sub.3                                                                          H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-CH.sub.3                                                                         CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-F     H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             4-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             5-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             6-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             5-Br    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             6-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             6-(CH.sub.3 ).sub.2 CH                                                                 H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             5-NO.sub.2                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             5-CH.sub.3 O                                                                           H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             5-CF.sub.3                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CH                                             5-OCOCH.sub.3                                                                          H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-CH.sub.3                                                                         CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                             5-F     H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             4-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             5-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             6-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             5-Br    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             6-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             5-NO.sub.2                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             5-CH.sub.3 O                                                                           H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             5-CF.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             5-OCOCH.sub.3                                                                          H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             3-Cl    5-CH.sub.3                                                                         CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                             5-F     H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              4-Cl    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              5-Cl    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              6-Cl    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              5-Br    H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              6-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              5-NO.sub.2                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              5-CH.sub.3 O                                                                           H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              5-CF.sub.3                                                                             H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              5-OCOCH.sub.3                                                                          H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              3-Cl    5-CH.sub.3                                                                         CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           N                                              5-F     H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              4-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              5-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              6-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              5-Br    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              6-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              5-NO.sub.2                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              5-CH.sub.3 O                                                                           H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              5-CF.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              5-OCOCH.sub.3                                                                          H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              3-Cl    5-CH.sub.3                                                                         CH.sub.3 CH.sub.3 O                                                                            CH.sub.3                                                                           N                                              5-F     H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              4-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              5-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              6-Cl    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              5-Br    H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              6-CH.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              5-NO.sub.2                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              5-CH.sub.3 O                                                                           H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              5-CF.sub.3                                                                             H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              5-OCOCH.sub.3                                                                          H   CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              3-Cl    5-CH.sub.3                                                                         CH.sub.3 CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                              H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCl                                            H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CBr                                            H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCN                                            H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.3                                      H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CC.sub.2 H.sub.5                               H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CH.sub.2 Cl                          H       H   CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CH.sub.2 CN                          Cl      Cl  CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCl                                            Cl      Cl  CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CBr                                            Cl      Cl  CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCN                                            Cl      Cl  CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.3                                      Cl      Cl  CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CC.sub.2 H.sub.5                               Cl      Cl  CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CH.sub.2 Cl                          Cl      Cl  CH.sub.3 CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CH.sub.2 CN                          H       H   CH.sub.3 H      CH.sub.3                                                                           CH                                             H       H   CH.sub.3 Cl     CH.sub.3                                                                           CH                                             H       H   CH.sub.3 Br     CH.sub.3                                                                           CH                                             H       H   CH.sub.3 C.sub. 2 H.sub.5                                                                      CH.sub.3                                                                           CH                                             H       H   CH.sub.3 CH.sub.3 (CH.sub.2).sub.2 O                                                           CH.sub.3                                                                           CH                                             H       H   CH.sub.3 CF.sub.3                                                                              CH.sub.3                                                                           CH                                             H       H   CH.sub.3 CH.sub.3 S                                                                            CH.sub.3                                                                           CH                                             H       H   CH.sub.3 CH.sub.3 OCH.sub.2                                                                    CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 H      CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 Cl     CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 Br     CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 C.sub.2 H.sub.5                                                                       CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3 (CH.sub.2).sub.2 O                                                           CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 CF.sub.3                                                                              CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3 S                                                                            CH.sub.3                                                                           CH                                             3-Cl    5-Cl                                                                               CH.sub.3 CH.sub.3 OCH.sub.2                                                                    CH.sub.3                                                                           CH                                             __________________________________________________________________________

                  TABLE IV                                                         ______________________________________                                          ##STR174##                                                                    R.sub.1   R.sub.2  R.sub.3   Y'      Q                                         ______________________________________                                         3-Cl      5-Cl     CH.sub.3  H       O                                         3-Cl      5-Cl     CH.sub.3  CH.sub.3                                                                               O                                         3-Cl      5-Cl     CH.sub.3  OCH.sub.3                                                                              O                                         3-Cl      5-Cl     CH.sub.3  Cl      O                                         3-Cl      5-Cl     CH.sub.3  H       CH.sub.2                                  3-Cl      5-Cl     CH.sub.3  CH.sub.3                                                                               CH.sub.2                                  3-Cl      5-Cl     CH.sub.3  OCH.sub.3                                                                              CH.sub.2                                  3-Cl      5-Cl     CH.sub.3  Cl      CH.sub.2                                  H         H        CH.sub.3  H       O                                         H         H        CH.sub.3  CH.sub.3                                                                               O                                         H         H        CH.sub.3  OCH.sub.3                                                                              O                                         H         H        CH.sub.3  Cl      O                                         H         H        CH.sub.3  H       CH.sub.2                                  H         H        CH.sub.3  CH.sub.3                                                                               CH.sub.2                                  H         H        CH.sub.3  OCH.sub.3                                                                              CH.sub.2                                  H         H        CH.sub.3  Cl      CH.sub.2                                  ______________________________________                                    

                                      TABLE V                                      __________________________________________________________________________      ##STR175##                                                                    R.sub.1 R.sub.2                                                                            R.sub.4      X      Y   Z                                          __________________________________________________________________________     H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H   CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H   CH.sub.2CHCH.sub.2                                                                          CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H   CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR176##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR177##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR178##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR179##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR180##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR181##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR182##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR183##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR184##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR185##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR186##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR187##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR188##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR189##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR190##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR191##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR192##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR193##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR194##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR195##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR196##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR197##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR198##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR199##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H                                                                                   ##STR200##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H   CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H   CH.sub.2CHCH.sub.2                                                                          CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H   CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR201##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR202##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR203##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR204##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR205##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR206##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR207##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR208##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR209##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR210##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR211##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR212##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR213##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR214##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR215##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR216##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR217##  CH.sub. 3                                                                             CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR218##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR219##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR220##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR221##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR222##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR223##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR224##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR225##  CH.sub.3                                                                              CH.sub.3 O                                                                         CH                                         H       H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H   CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H   CH.sub.2CHCH.sub.2                                                                          CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H   CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR226##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR227##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR228##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR229##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR230##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR231##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR232##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR233##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR234##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR235##  CH.sub. 3 O                                                                           CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR236##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR237##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR238##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR239##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR240##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR241##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR242##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR243##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR244##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR245##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR246##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR247##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR248##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR249##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H                                                                                   ##STR250##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H   CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H   CH.sub.2CHCH.sub.2                                                                          CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H   CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR251##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR252##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR253##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR254##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR255##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR256##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR257##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR258##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR259##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR260##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR261##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR262##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR263##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR264##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR265##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR266##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR267##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR268##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR269##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR270##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR271##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR272##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR273##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR274##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H                                                                                   ##STR275##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          H       H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H   CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H   CH.sub.2CHCH.sub.2                                                                          CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H   CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR276##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR277##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR278##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR279##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR280##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR281##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR282##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR283##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR284##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR285##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR286##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR287##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR288##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR289##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR290##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR291##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR292##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR293##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR294##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR295##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR296##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR297##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR298##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR299##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H                                                                                   ##STR300##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          H       H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H   CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H   CH.sub.2CHCH.sub.2                                                                          CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H   CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR301##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR302##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR303##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR304##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR305##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR306##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR307##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR308##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR309##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR310##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR311##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR312##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR313##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR314##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR315##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR316##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR317##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR318##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR319##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR320##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR321##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR322##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR323##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR324##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H                                                                                   ##STR325##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                          CH.sub. 3                                                                             CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR326##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR327##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR328##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR329##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR330##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR331##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR332##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR333##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR334##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR335##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR336##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR337##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR338##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR339##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR340##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR341##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR342##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR343##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR344##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR345##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR346##  CH.sub.3                                                                              CH.sub. 3                                                                          CH                                         3-Cl    5-Cl                                                                                ##STR347##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR348##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR349##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR350##  CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                          CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR351##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR352##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR353##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR354##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR355##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR356##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR357##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR358##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR359##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR360##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR361##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR362##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR363##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR364##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR365##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR366##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR367##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR368##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR369##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR370##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR371##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR372##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR373##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR374##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                                ##STR375##  CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                          CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                               CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR376##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR377##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR378##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR379##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR380##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR381##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR382##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR383##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR384##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR385##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR386##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR387##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR388##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR389##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR390##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR391##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR392##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR393##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR394##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR395##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR396##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR397##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR398##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR399##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                                ##STR400##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                          CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                               CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR401##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR402##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR403##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR404##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR405##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR406##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR407##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR408##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR409##  CH.sub.3                                                                              CH.sub. 3                                                                          N                                          3-Cl    5-Cl                                                                                ##STR410##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR411##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR412##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR413##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR414##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR415##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR416##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR417##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR418##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR419##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR420##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR421##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR422##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR423##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR424##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR425##  CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                          CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                               CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR426##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR427##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR428##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR429##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR430##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR431##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR432##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR433##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR434##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR435##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR436##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR437##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR438##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR439##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR440##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR441##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR442##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR443##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR444##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR445##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR446##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR447##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR448##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR449##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                                ##STR450##  CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.5                                                                   CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                               CH.sub.2CHCH.sub.2                                                                          CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                               CH.sub.3 CHCHCH.sub.2                                                                       CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR451##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR452##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR453##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR454##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR455##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR456##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR457##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR458##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR459##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR460##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR461##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR462##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR463##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR464##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR465##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR466##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR467##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR468##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR469##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR470##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR471##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR472##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR473##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR474##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-Cl                                                                                ##STR475##  CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          5-F     H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         4-Cl    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         5-Cl    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         6-Cl    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         5-Br    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         6-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         5-NO.sub.2                                                                             H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         5-CH.sub.3 O                                                                           H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         5-CF.sub.3                                                                             H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         5-OCOCH.sub.3                                                                          H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-CH.sub.3                                                                         CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CH                                         5-F     H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         4-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         5-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         6-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         5-Br    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         6-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         5-NO.sub.2                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         5-CH.sub.3 O                                                                           H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         5-CF.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         5-OCOCH.sub.3                                                                          H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-CH.sub.3                                                                         CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                         5-F     H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         4-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         5-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         6-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         5-Br    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         6-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         5-NO.sub.2                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         5-CH.sub.3 O                                                                           H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         5-CF.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         5-OCOCH.sub.3                                                                          H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         3-Cl    5-CH.sub.3                                                                         CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                         5-F     H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          4-Cl    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          5-Cl    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          6-Cl    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          5-Br    H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          6-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          5-NO.sub.2                                                                             H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          5-CH.sub.3 O                                                                           H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          5-CF.sub.3                                                                             H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          5-OCOCH.sub.3                                                                          H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          3-Cl    5-CH.sub.3                                                                         CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           N                                          5-F     H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          4-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          5-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          6-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          5-Br    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          6-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          5-NO.sub.2                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          5-CH.sub.3 O                                                                           H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          5-CF.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          5-OCOCH.sub.3                                                                          H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          3-Cl    5-CH.sub.3                                                                         CH.sub.3     CH.sub.3 O                                                                            CH.sub.3                                                                           N                                          5-F     H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          4-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          5-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          6-Cl    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          5-Br    H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          6-CH.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          5-NO.sub.2                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          5-CH.sub.3 O                                                                           H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          5-CF.sub.3                                                                             H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          5-OCOCH.sub.3                                                                          H   CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          3-Cl    5-CH.sub.3                                                                         CH.sub.3     CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                          H       H   CH.sub.3     H      CH.sub.3                                                                           CH                                         H       H   CH.sub.3     Cl     CH.sub.3                                                                           CH                                         H       H   CH.sub.3     Br     CH.sub.3                                                                           CH                                         H       H   CH.sub.3     C.sub.2 H.sub.5                                                                       CH.sub.3                                                                           CH                                         H       H   CH.sub.3     CH.sub.3 (CH.sub.2).sub.2 O                                                           CH.sub.3                                                                           CH                                         H       H   CH.sub.3     CF.sub.3                                                                              CH.sub.3                                                                           CH                                         H       H   CH.sub.3     CH.sub.3 S                                                                            CH.sub.3                                                                           CH                                         H       H   CH.sub.3     CH.sub.3 OCH.sub.2                                                                    CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     H      CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     Cl     CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     Br     CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     C.sub.2 H.sub.5                                                                       CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3 (CH.sub.2).sub.2 O                                                           CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     CF.sub.3                                                                              CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3 S                                                                            CH.sub.3                                                                           CH                                         3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3 OCH.sub.2                                                                    CH.sub.3                                                                           CH                                         H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCl                                        H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CBr                                        H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCN                                        H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.3                                  H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CC.sub.2 H.sub.5                           H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CH.sub.2 Cl                      H       H   CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CHCH.sub.2                       3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCl                                        3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CBr                                        3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCN                                        3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.3                                  3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CC.sub.2 H.sub.5                           3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CH.sub.2 Cl                      3-Cl    5-Cl                                                                               CH.sub.3     CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CHCH.sub.2                       __________________________________________________________________________

                  TABLE VI                                                         ______________________________________                                          ##STR476##                                                                    R.sub.1  R.sub.2   R.sub.4   Y'       Q                                        ______________________________________                                         3-Cl     5-Cl      CH.sub.3  H        O                                        3-Cl     5-Cl      CH.sub.3  CH.sub.3 O                                        3-Cl     5-Cl      CH.sub.3  OCH.sub.3                                                                               O                                        3-Cl     5-Cl      CH.sub.3  Cl       O                                        3-Cl     5-Cl      CH.sub.3  H        CH.sub.2                                 3-Cl     5-Cl      CH.sub.3  CH.sub.3 CH.sub.2                                 3-Cl     5-Cl      CH.sub.3  OCH.sub.3                                                                               CH.sub.2                                 3-Cl     5-Cl      CH.sub.3  Cl       CH.sub.2                                 H        H         CH.sub.3  H        O                                        H        H         CH.sub.3  CH.sub.3 O                                        H        H         CH.sub.3  OCH.sub.3                                                                               O                                        H        H         CH.sub.3  Cl       O                                        H        H         CH.sub.3  H        CH.sub.2                                 H        H         CH.sub.3  CH.sub.3 CH.sub.2                                 H        H         CH.sub.3  OCH.sub.3                                                                               CH.sub.2                                 H        H         CH.sub.3  Cl       CH.sub.2                                 ______________________________________                                    

                                      TABLE VII                                    __________________________________________________________________________      ##STR477##                                                                    R.sub.1 R.sub.2                                                                            R.sub.5 X      Y   Z                                               __________________________________________________________________________     H       H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              H       H   CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR478##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR479##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR480##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR481##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR482##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              H       H   CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR483##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR484##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR485##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR486##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              H       H                                                                                   ##STR487##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               H       H   CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               H       H                                                                                   ##STR488##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               H       H                                                                                   ##STR489##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               H       H                                                                                   ##STR490##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               H       H                                                                                   ##STR491##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               H       H                                                                                   ##STR492##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               H       H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               H       H   CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               H       H                                                                                   ##STR493##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               H       H                                                                                   ##STR494##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               H       H                                                                                   ##STR495##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               H       H                                                                                   ##STR496##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               H       H                                                                                   ##STR497##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR498##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR499##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR500##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR501##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR502##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR503##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR504##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR505##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR506##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                                ##STR507##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    5-Cl                                                                                ##STR508##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    5-Cl                                                                                ##STR509##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    5-Cl                                                                                ##STR510##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    5-Cl                                                                                ##STR511##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    5-Cl                                                                                ##STR512##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR513##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR514##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR515##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR516##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR517##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                               CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR518##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR519##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR520##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR521##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                                ##STR522##                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    5-Cl                                                                               CH.sub. 3 (CH.sub.2).sub.4                                                             CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    5-Cl                                                                                ##STR523##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    5-Cl                                                                                ##STR524##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    5-Cl                                                                                ##STR525##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    5-Cl                                                                                ##STR526##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    5-Cl                                                                                ##STR527##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               5-F     H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              4-Cl    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              5-Cl    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              6-Cl    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              5-Br    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              6-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              5-NO.sub. 2                                                                            H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              5-CH.sub.3 O                                                                           H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              5-CF.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              5-OCOCH.sub.3                                                                          H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCl                                             H       H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CBr                                             H       H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCN                                             H       H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.3                                       H       H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CC.sub.2 H.sub.5                                H       H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CH.sub.2 Cl                           H       H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CHCH.sub.2                            3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCl                                             3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CBr                                             3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCN                                             3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.3                                       3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CC.sub.2 H.sub.5                                3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CH.sub. 2 Cl                          3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           CCH.sub.2 CHCH.sub.2                            H       H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              H       H   CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              H       H                                                                                   ##STR528##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              H       H                                                                                   ##STR529##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              H       H                                                                                   ##STR530##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              H       H                                                                                   ##STR531##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              H       H                                                                                   ##STR532##                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              H       H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               H       H   CH.sub.3 (CH.sub.2).sub.4                                                              CH.sub.3                                                                              CH.sub.3                                                                           N                                               H       H                                                                                   ##STR533##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               H       H                                                                                   ##STR534##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               H       H                                                                                   ##STR535##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               H       H                                                                                   ##STR536##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               H       H                                                                                   ##STR537##                                                                            CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-F     H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              4-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              5-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              6-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              5-Br    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              6-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              5-NO.sub.2                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              5-CH.sub.3 O                                                                           H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              5-CF.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              5-OCOCH.sub.3                                                                          H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           CH                                              5-F     H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              4-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              5-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              6-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              5-Br    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              6-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              5-NO.sub.2                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              5-CH.sub.3 O                                                                           H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              5-CF.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              5-OCOCH.sub.3                                                                          H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              3-Cl    5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         CH                                              5-F     H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               4-Cl    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-Cl    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               6-Cl    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-Br    H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               6-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-NO.sub.2                                                                             H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-CH.sub.3 O                                                                           H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-CF.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-OCOCH.sub.3                                                                          H   CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               3-Cl    5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                           N                                               5-F     H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    H   CH.sub. 3                                                                              CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               4-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               5-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               6-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               5-Br    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               6-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               5-NO.sub.2                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               5-CH.sub.3 O                                                                           H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               5-CF.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               5-OCOCH.sub.3                                                                          H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               3-Cl    5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3                                                                           N                                               5-F     H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               4-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               5-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               6-Cl    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               5-Br    H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               6-CH.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               6-(CH.sub.3).sub.2 CH                                                                  H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               5-NO.sub.2                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               5-CH.sub.3 O                                                                           H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               5-(CH.sub.3).sub.2 CHO                                                                 H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               5-CF.sub.3                                                                             H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               5-OCOCH.sub.3                                                                          H   CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-CH.sub.3                                                                             5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               3-Cl    5-CH.sub.3                                                                         CH.sub.3                                                                               CH.sub.3 O                                                                            CH.sub.3 O                                                                         N                                               H       H   CH.sub.3                                                                               H      CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               Cl     CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               Br     CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               C.sub.2 H.sub.5                                                                       CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               CH.sub.3 (CH.sub.2).sub.2 O                                                           CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               CF.sub.3                                                                              CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               CH.sub.3 S                                                                            CH.sub.3                                                                           CH                                              H       H   CH.sub.3                                                                               CH.sub.3 OCH.sub.2                                                                    CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               H      CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               Cl     CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               Br     CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               C.sub.2 H.sub.5                                                                       CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3 (CH.sub.2).sub.2 O                                                           CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               CF.sub.3                                                                              CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3 S                                                                            CH.sub.3                                                                           CH                                              3-Cl    5-Cl                                                                               CH.sub.3                                                                               CH.sub.3 OCH.sub.2                                                                    CH.sub.3                                                                           CH                                              __________________________________________________________________________

                  TABLE VIII                                                       ______________________________________                                          ##STR538##                                                                    R.sub.1  R.sub.2   R.sub.5   Y'       Q                                        ______________________________________                                         3-Cl     5-Cl      CH.sub.3  H        O                                        3-Cl     5-Cl      CH.sub.3  CH.sub.3 O                                        3-Cl     5-Cl      CH.sub.3  OCH.sub.3                                                                               O                                        3-Cl     5-Cl      CH.sub.3  Cl       O                                        3-Cl     5-Cl      CH.sub.3  H        CH.sub.2                                 3-Cl     5-Cl      CH.sub.3  CH.sub.3 CH.sub.2                                 3-Cl     5-Cl      CH.sub.3  OCH.sub.3                                                                               CH.sub.2                                 3-Cl     5-Cl      CH.sub.3  Cl       CH.sub.2                                 H        H         CH.sub.3  H        O                                        H        H         CH.sub.3  CH.sub.3 O                                        H        H         CH.sub.3  OCH.sub.3                                                                               O                                        H        H         CH.sub.3  Cl       O                                        H        H         CH.sub.3  H        CH.sub.2                                 H        H         CH.sub.3  CH.sub.3 CH.sub.2                                 H        H         CH.sub.3  OCH.sub.3                                                                               CH.sub.2                                 H        H         CH.sub.3  Cl       CH.sub.2                                 ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE IX                                                         ______________________________________                                                     Active*                                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90     0-74      1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solu-                                                               tions (including                                                               Emulsifiable                                                                   Concentrates                                                                   Aqueous Suspensions                                                                          10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and  0.1-95      5-99.9  0-15                                         Pellets                                                                        High-Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at least one of a surfactant or a diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 1, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 5, line 66 through Col. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 3 Wettable Powder

    ______________________________________                                         3,5-dichloro-N--[(4,6-dimethoxypyrimi-                                                                80%                                                     din-2-yl)aminocarbonyl]-2-hydroxy-                                             benzenesulfonamide, acetate                                                    sodium alkylnaphthalenesulfonate                                                                      2%                                                      sodium ligninsulfonate 2%                                                      synthetic amorphous silica                                                                            3%                                                      kaolinite              13%                                                     ______________________________________                                    

The ingredients are blended, hammer-milled until the solids are substantially under 50 microns and then reblended.

EXAMPLE 4 Wettable Powder

    ______________________________________                                         3,5-dichloro-N--[(4,6-dimethypyrimidin-                                                               50%                                                     2-yl)aminocarbonyl]-2-hydroxybenzene-                                          sulfonamide, acetate                                                           sodium alkylnaphthalenesulfonate                                                                      2%                                                      low-viscosity methyl cellulose                                                                        2%                                                      diatomaceous earth     46%                                                     ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles of active substantially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 5 Granule

    ______________________________________                                         wettable powder of Example 4                                                                         5%                                                       attapulgite granules  95%                                                      (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 6 Extruded Pellet

    ______________________________________                                         3,5-dichloro-2-hydroxy-N--[(4-methoxy-                                                                 25%                                                    6-methyl-pyrimidin-2-yl)aminocarbonyl]-                                        benzenesulfonamide, acetate                                                    anhydrous sodium sulfate                                                                               10%                                                    crude calcium ligninsulfonate                                                                           5%                                                    sodium alkylnaphthalenesulfonate                                                                        1%                                                    calcium/magnesium bentonite                                                                            59%                                                    ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 7 Oil Suspension

    ______________________________________                                         3,5-dichloro-N--[(4,6-dimethoxypyri-                                                                  25%                                                     midin-2-yl)aminocarbonyl]-2-hydroxy-                                           benzenesulfaonamide, acetate                                                   polyoxyethylene sorbitol hexaoleate                                                                    5%                                                     highly aliphatic hydrocarbon oil                                                                      70%                                                     ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 8 Wettable Powder

    ______________________________________                                         3,5-dichloro-2-hydroxy-N--[(4-methoxy-                                                                20%                                                     6-methyl-pyrimidin-2-yl)aminocar-                                              bonyl]benzenesulfonamide, acetate                                              sodium alkylnaphthalenesulfonate                                                                      4%                                                      sodium ligninsulfonate 4%                                                      low-viscosity methyl cellulose                                                                        3%                                                      attapulgite            69%                                                     ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles substantially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 9 Low-Strength Granule

    ______________________________________                                         3,5-dichloro-2-hydroxy-N--[(4-methoxy-                                                                    1%                                                  6-methyl-pyrimidin-2-yl)aminocar-                                              bonyl]benzenesulfonamide, acetate                                              N,N--dimethylformamide     9%                                                  attapulgite granules       90%                                                 (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 10 Aqueous Suspension

    ______________________________________                                         3,5-dichloro-N--[(4,6-dimethylpyrimi-                                                                    40%                                                  din-2-yl)aminocarbonyl]-2-hydroxy-                                             benzenesulfonamide, acetate                                                    polyacrylic acid thickener                                                                               0.3%                                                 dodecylphenol polyethylene glycol                                              ether                     0.5%                                                 disodium phosphate        1%                                                   monosodium phosphate      0.5%                                                 polyvinyl alcohol         1.0%                                                 Water                     56.7%                                                ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles substantially all under 5 microns in size.

EXAMPLE 11 Solution

    ______________________________________                                         3,5-dichloro-2-hydroxy-N--[(4-methoxy-                                                                    5%                                                  6-methyl-pyrimidin-2-yl)aminocar-                                              bonyl]benzenesulfonamide, acetate                                              sodium salt                                                                    water                      95%                                                 ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 12 Low-Strength Granule

    ______________________________________                                         3,5-dichloro-N--[(4,6-dimethoxypyri-                                                                     0.1%                                                 midin-2-yl)aminocarbonyl]-2-hydroxy-                                           benzenesulfonamide, acetate                                                    attapulgite granules      99.9%                                                (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 13 Granule

    ______________________________________                                         3,5-dichloro-2-hydroxy-N--[(4-methoxy-                                                                    80%                                                 6-methyl-pyrimidin-2-yl)aminocarbon-                                           yl]benzenesulfonamide, acetate                                                 wetting agent              1%                                                  crude ligninsulfonate salt (containing                                                                    10%                                                 5-20% of the natural sugars)                                                   attapulgite clay           9%                                                  ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water constant is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 14 High-Strength Concentrate

    ______________________________________                                         3,5-dichloro-N--[(4,6-dimethoxy-                                                                          99%                                                 pyrimidin-2-yl)aminocarbonyl]-2-                                               hydroxybenzenesulfonamide, acetate                                             silica aerogel             0.5%                                                synthetic amorphous silica 0.5%                                                ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material substantially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 15 Wettable Powder

    ______________________________________                                         3,5-dichloro-N--[(4,6-dimethylpyrimidin-                                                               90.0%                                                  2-yl)aminocarbonyl]-2-hydroxybenzene-                                          sulfonamide, acetate                                                           dioctyl sodium sulfosuccinate                                                                          0.1%                                                   synthetic fine silica   9.9%                                                   ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles substantially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 16 Wettable Powder

    ______________________________________                                         3,5-dichloro-2-hydroxy-N--[(4-methoxy-                                                                 40%                                                    6-methyl-pyrimidin-2-yl)aminocarbon-                                           yl]benzenesulfonamide, acetate                                                 sodium ligninsulfonate  20%                                                    montmorillonite clay    40%                                                    ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles substantially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 17 Dust

    ______________________________________                                         3,5-dichloro-N--[(4,6-dimethoxypyrimi-                                                                 10%                                                    din-2-yl)aminocarbonyl]-2-hydroxy-                                             benzenesulfonamide, acetate                                                    attapulgite             10%                                                    pyrophyllite            80%                                                    ______________________________________                                    

The active ingredient is blended with attapulgite and then passed through a hammer mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

Utility

The compounds of the present invention are active herbicides. They have utility for broad spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil-well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate and time of application, compounds of this invention may be used to modify plant growth beneficially, and also selectively control weeds in crops such as wheat, rice, corn, and various leguminous crops.

The precise amount of the compound of Formula I to be used in any given situation will vary according to the particular end result desired, the amount of foliage present, the weeds to be controlled, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situations. Broadly speaking, the compounds of this invention are used at levels of about 0.01 to 20 kg/ha with a preferred range of 0.1 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired.

The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with 3-(3,4-dichlorophenyl)-1,1-dimethylurea (diuron); the triazines such as 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine (atrazine); the uracils such as 5-bromo-3-sec-butyl-6-methyluracil (bromacil); N-(phosponomethyl)glycine (glyphosate); 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione (hexazinone); N,N-dimethyl-2,2-diphenylacetamide (diphenamide); 2,4-dichlorophenoxyacetic acid (2,4-D) (and closely related compounds); 4-chloro-2-butynyl-3-chlorophenylcarbamate (barban); S-(2,3-dichloroallyl)diisopropylthiocarbamate (diallate); S-(2,3,3-trichloroallyl)diisopropylthiocarbamate (triallate); 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (difenzoquat methyl sulfate); methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate (diclofop methyl); 4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)one (metribuzin); 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (linuron); 3-isopropyl-1H-2,1,3-benzothiodiazin-4(3H)-one-2,2-dioxide (bentazon); α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (trifluralin); 1,1'-dimethyl-4,4'-bipyridinium ion (paraquat); 2-chloro-2',6'-diethyl(methoxymethyl)acetanilide (alachlor); 1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea (fluometuron), S-(4-chlorobenzyl)N,N-diethylthiolcarbamate (benthiocarb); and N-(butoxymethyl)-2-chloro-2',6'-diethylacetanilide (butachlor).

The activity of these compounds was discovered in greenhouse tests. The tests are described and the data resulting from them are shown below.

TEST PROCEDURE

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua, Cassia tora, morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers were planted in a growth medium and treated preemergence with the chemicals dissolved in a nonphytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliolate leaf expanding, crabgrass with two leaves, barnyardgrass with two leaves, wild oats with one leaf, cassia with three leaves (including cotyledonary ones), morningglory with four leaves (including the cotyledonary ones), sorghum with three leaves, corn with three leaves, soybean with two cotyledonary leaves, rice with two leaves, wheat with one leaf, and nutsedge with three-fives leaves were sprayed. Treated plants and controls were maintained in a greenhouse for 16 days, then all species were compared to controls and visually rated for response to treatment.

Ratings for compounds tested by this procedure are recorded in Table A.

0=no effect

& or 10=maximum effect

B=burn

C=chlorosis or necrosis

G=growth retardation

H=formative effects

                                      TABLE A                                      __________________________________________________________________________                  ##STR539##                                                                                            ##STR540##                                             kg/ha                                                                                    2/5                   2/5                                __________________________________________________________________________     POST-EMERGENCE                                                                 BUSHBEAN              1C,1H                 1C,1H                              COTTON                2C,9G                 2B,4H,9G                           MORNINGGLORY          5H                    5H                                 COCKLEBUR             8H                    5G                                 CASSIA                2H                    4G                                 NUTSEDGE              0                     0                                  CRABGRASS             1B                    0                                  BARNYARDGRASS         1B                    0                                  WILD OATS             0                     0                                  WHEAT                 0                     0                                  CORN                  1C,5H                 0                                  SOYBEAN               1H,4G                 3H                                 RICE                  0                     2G                                 SORGHUM               3G                    4H                                 PRE-EMERGENCE                                                                  MORNINGGLORY          8H                    5G                                 COCKLEBUR             8H                    8G                                 CASSIA                7G                    7G                                 NUTSEDGE              5G                    0                                  CRABGRASS             0                     0                                  BARNYARDGRASS         2C,5G                 0                                  WILD OATS             2G                    0                                  WHEAT                 0                     0                                  CORN                  2G                    2G                                 SOYBEAN               0                     2G                                 RICE                  7H                    2G                                 SORGHUM               2G                    4G                                 __________________________________________________________________________ 

What is claimed is:
 1. A compound selected from: ##STR541## wherein P is ##STR542## R₁ is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, C₁ -C₃ alkoxy, CF₃ or ##STR543## R₂ is H, CH₃ or Cl; R₃ is H; C₁ -C₅ alkyl; C₂ -C₃ alkenyl; C₂ -C₃ alkynyl; C₁ -C₄ alkyl substituted with 1-3 substituents selected from 0-3 F, 0-3 Cl, 0-3 Br, and OCH₃ ; C₂ -C₃ alkenyl substitutd with Cl; C₃ -C₆ cycloalkyl; or ##STR544## R₄ is C₁ -C₆ alkyl; C₃ -C₄ alkenyl; C₃ -C₆ cycloalkyl; C₅ -C₆ cycloalkyl substituted with CH₃ ; ##STR545## R₅ is C₁ -C₆ alkyl or ##STR546## R₆ and R₇ are independently H, NO₂, CH₃, Cl or OCH₃ ;R₈ is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, CN, SO₂ CH₃, OCH₃, SCH₃ or CF₃ ; R₉ is H or C₁ -C₃ alkyl; R₁₀ is H, CH₃ or Cl; A is ##STR547## X is H, Cl, Br, CH₃, CH₃ CH₂, C₁ -C₃ alkoxy, CF₃, CH₃ S or CH₃ OCH₂ ; Y is CH₃ or CH₃ o; Z is N, CH, C--Cl, C--Br, C--CN, C--CH₃, --C--CH₂ CH₃, C--CH₂ CH₂ Cl or C--CH₂ CH═CH₂ ; Y' is H, CH₃, OCH₃ or Cl; and Q is O or CH₂ ;and their agriculturally suitable salts.
 2. A compound of claim 1 wherein Z is N, CH, C--Cl, C--CN, C--Br or C--CH₃.
 3. A compound of claim 2 where Z is CH or N and X is CH₃ or OCH₃.
 4. A compound of claim 3 where A is ##STR548##
 5. A compound of claim 4 where R₁ is H.
 6. A compound of claim 5 where R₂ is H.
 7. A compound of claim 6 where R₃, R₄ and R₅ are C₁ -C₃ alkyl.
 8. A compound selected from: ##STR549## wherein R₁ is H, F, Cl, Br, C₁ -C₃ alkyl, NO₂, C₁ -C₃ alkoxy, CF₃ or ##STR550## R₂ is H, CH₃ or Cl; A is ##STR551## X is H, Cl, Br, CH₃, CH₃ CH₂, C₁ -C₃ alkoxy, CF₃, CH₃ S or CH₃ OCH₂ ;Y is CH₃ or CH₃ O; Z is N, CH, C--Cl, C--Br, C--CN, C--CH₃, --C--CH₂ CH₃, C--CH₂ CH₂ Cl or C--CH₂ CH═CH₂ ; Y' is H, CH₃, OCH₃ or Cl; and Q is O or CH₂ ;
 9. The compound of claim 8, 3,5-dichloro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide.
 10. The compound of claim 8, 3,5-dichloro-2-hydroxy-N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.
 11. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 1 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
 12. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 2 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
 13. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 3 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
 14. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 4 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
 15. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 5 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
 16. A composition for the control of undesirable vegetation consisting essentially of a compound of claim 6 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
 17. A method for the control of undesirable vegetation consisting of applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim
 1. 18. A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim
 2. 19. A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim
 3. 20. A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim
 4. 21. A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim
 5. 22. A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim
 6. 